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Redefining Ambition
For those disinterested in the corporate ladder
Today’s edition of Wishful Working is a 3 minute read.
I have what one might describe as a complicated relationship with the concept of ambition. In the spirit of the high school commencement speech, allow me to provide the dictionary definition of the word ambitious:
1. having a desire to be successful, powerful, or famous
Synonyms include words like energetic, eager, go-getting, and hard-driving.
As a little experiment, I asked an AI image generator for a picture of an “ambitious woman.”
“Ambitious Woman”
Funny enough, this is the exact image my brain creates when I think about ambition embodied.
She’s in a conference room, in a high rise. She’s wearing business clothes. She has a fancy briefcase. She’s serious. She’s corporate. (And she probably makes less than 80% what a White man would make in her role, just saying.)
I have never identified with this particular brand of ambition.
In my (admittedly, relatively brief) “employee era,” I never pursued promotions or aspired to management. I honestly often felt I wasn’t even cut out for my junior-level, individual contributor roles.
Something always felt off.
Maybe I’m just not good at this, I concluded. This being work, in the broadest sense. I thought I lacked some essential drive that everyone else had. I thought maybe I was just lazy.
That’s not a great feeling to have.
By the time I left my most recent “regular” job in 2021, my feelings toward work were a roiling witch’s brew: a dash of imposter syndrome, a heaping handful of burnout, and a simmering discontentment bubbling beneath it all.
Mercifully, life circumstances provided a much needed, multi-month sabbatical to work through this existential crisis. And when I came out on the other side, I was a newly-minted freelancer.
It hasn’t been easy, but over the past two years, I’ve seen and felt things clicking into place.
I’m not unambitious, I’m just disinterested in climbing a predefined ladder of success on someone else’s terms.
I’m not lazy, I’m just dialed-in to my energy, and I respect my body’s natural rhythms (now that I’m allowed to).
The other day, this quote (often attributed to Albert Einstein, but I don’t think we really know where it came from) came to mind:
Everyone is a genius. But if you judge a fish by its ability to climb a tree, it will live its whole life believing that it is stupid.
In other words:
Everyone is ambitious. But if you judge a person with an independent, entrepreneurial mindset by her ability to thrive in a traditional, hierarchical workplace, she will live her life believing she is lazy.
🤯
Although imposter syndrome and burnout still show up from time to time, I feel a confidence and a sure-footedness in my work that I previously didn’t know was possible.
And if we circle back to the word “ambitious,” there’s actually a second definition 😉
2. having a desire to achieve a particular goal
By this definition, my ambition doesn’t need to be aimed at success, power, or fame. It can instead be aimed at goals I define: peace, rest, balance, simplicity, creativity.
That’s more like it.

“Ambitious Woman”
See you next week,
Kara